


Damn Pirates

by Scytheress



Category: Supernatural
Genre: Alternate Universe - Pirate, Case Fic, F/M, I have no idea what I'm doing, M/M, More tags will be added as things go along, Multi, Pirates, Protective Dean Winchester, Sick Sam Winchester, Slow Burn, Yes they will all be pirates eventually, kind of, kraken - Freeform
Language: English
Status: In-Progress
Published: 2018-06-13
Updated: 2018-07-11
Packaged: 2019-05-21 14:39:58
Rating: Mature
Warnings: Graphic Depictions Of Violence, Major Character Death, Underage
Chapters: 6
Words: 14,509
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14917241
Author URL: https://archiveofourown.org/users/Scytheress/pseuds/Scytheress
Summary: Dean and Sam have been long-time residents of Port Royal, living in back alleys and surviving mostly on perseverance and luck. A chance encounter at sea changes everything and soon the fisherman and scholar will find themselves embroiled in one of the greatest pirate wars the Caribbean has ever seen. (Loosely follows Pirates of the Caribbean but with a case!fic twist. Who wants to hunt a kraken?)





	1. Just Fishing

**Author's Note:**

> So I have not written in a very long time and it shows. This is un-beta'd but if anyone reads this and thinks, "Great idea! But uh, your phrasing..." and wants to give me a hand, hit up my inbox and I'll love you forever.  
> Also, I don't have an update schedule for this yet. I could lay out the excuses of why updating might be sporadic but I won't.

_“Dean...”_

_The blonde's eyes fell closed as he tightening his grip on the back of the other man's vest. The other man was turned away from him, glancing out into the veil of grey fog and standing stiffly in the late autumn rain. Dean drew his lower lip between his teeth, unsure if he was biting down to keep his teeth from chattering or to stem the sob he felt welling in his throat. His attempts to fortify his mental state were shattered by the deep voice before him._

_“I have to go.”_

_"No!" tore itself from Dean's throat. As much as he wished his protest would be heeded, the only response he received was the other man tensing beyond his touch . Dean's chest shuddered with the next inhalation of frigid air and he grit his teeth. He tried to will his lungs to cooperate before he cast his eyes up, once more, at the back of the dark haired man. “You can't leave me.”_

_The shadowed man bowed his head and let out a short breath as if he'd been punched._

_“Dean, I'll hang.”_

_Dean rubbed the coarse fabric between his thumb and index finger. “Then we'll run. We can leave.”_

_“And Sam?” the other questioned, turning his head to the side, not quite glancing over his shoulder._

_"Sam..." Dean's hand clutched tighter, pulling the vest and shirt underneath flush against the other man's ribs._

_“That boy wouldn't survive without you and you know he's in no condition to travel. He needs you, Dean.”_

_The blonde's eyes turned to the mud growing between their feet as his hand fell back to his side._

_Dean's tone began to waiver, “You can't...”_

_“I have to,” the gravely voice interrupted._

_“But -”_

_“Goodbye, Dean.”_

~*~  
“Cas!”

Dean bolted upright in bed with the taste of a ghost's name on his lips. Gasping and trying to regain his breath, he brought his hands up to his face to wipe away the sweat he felt beaded on his skin. He would always insist it was just sweat. It had been 10 years since he last saw Castiel and he had no more tears to shed over that man. They had made their choice and there was never going to be any going back.

The blonde managed to steady his breathing just in time for a sharp clank from beyond his door to jolt his lungs into painful stillness. His first look was to the empty space beside him.  _Sammy_. And his next back to the door, ears straining to make out any sounds of struggle. Instead, muted cursing floated from the kitchen to prove his brain was overreacting as usual. If he had to hazard a guess now that his heart wasn't about to jump from his chest, Sam was just already up and making breakfast. More like wreaking havoc on the small stove than actually cooking, but making breakfast nonetheless.

Dean pulled the sheets back from his legs and achily got out of bed, scratching the short stubble on his chin and then rubbing at his eyes again before exiting his room in naught but his pants. Instantly, he felt better when he saw his little brother crouched a few feet away. Safe. To shake off the heavy feeling in his chest, Dean stretched dramatically with his arms over his head, his stomach pulled taught, and let out the most ridiculous sounding fake yawn he could muster. Sam stifled a laugh and rolled his eyes before looking up from the pot over the fire pit with a grin - a grin that faded quickly into a small, knowing smile when their gazes met. To Dean's surprise, Sam was fully dressed with his hair pulled back in a low pony tail like he was getting ready to leave but before Dean had a chance to ask why he already had his shoes on, Sam passed him a bowl containing some of whatever was in the pot. Dean was about to thank him for the meal but he should have known his brother was too perceptive for his own good.

“You haven't had that dream in a while. You alright?”

Dean inwardly grimaced and shrugged as he accepted the bowl. He was used to nightmares. He'd been having them ever since Cas left. It had started with worst case scenarios - the guards had caught him before he reached the docks, or his new captain discovered who he really was, or Cas' ship ran into pirates, any number of tragic endings . It wasn't until word that the ship Cas had signed on to crew went down in the hurricane that Dean started dreaming of the last night he saw him alive and those were the ones that hit him the hardest. 

Dean quickly shook off the somber expression that threatened to to bring Sam's full concern down on him and tilted his bowl curiously, “I'm fine but, uh, what is this?”

Sam smirked and went back to stirring the pot, “Breakfast stew.”

He raised an eyebrow, “And what's breakfast stew?”

“Dinner stew, but reheated in the morning.”

Dean chuckled at that and went in search of a spoon. As he passed his little brother, he ruffled Sam's hair right out of the leather tie that held it back, earning a hard slap to his thigh for his efforts. Sam huffed as he gathered his hair again to bind it practically behind his head before scooping himself a serving from the pot. He sat back on one of the two stumps around the fire pit to eat.

After a bite, he looked to his brother, “So, back to the docks today?”

A cry of success heralded Dean's finding of a spoon before he came back and sat opposite Sam.

“Of course, the fish aren't going to catch themselves.” He shoveled a large bite of stew into his mouth.

“You know,” Sam looked down at his bowl pensively, “I could go with you. I could help.”

“Sammy,” Dean swallowed and set his bowl down, exhaustion already evident in his tone. So this was why he was ready to leave so early. Dean leaned forward and propped his elbows on his knees, clasping his hands together loosely as he peered across the fire at his brother, “You know you're not supposed to be outside too much. What if -”

“What if nothing, Dean.” Sam snapped back and narrowed his eyes. Dean could already see the resolute frustration creasing his brother's brow. “It's been years, YEARS, since my last episode. I'm fine and you know it. And God knows we could use the extra money.” He gestured vaguely to the rest of their small shack, at the bullets of light dotting the floor from holes in the roof, at the lack of any real furniture.

Dean lowered his head to card his hands through his hair, trying to soothe himself and remain calm. He'd had this conversation with Sam dozens of times but after the dream he'd had he just couldn't relent. It was true, Sam hadn't had an episode in three years, when he was 19, but the last time he'd had a sudden headache he'd fallen off his horse, broken his wrist, and been unconscious for 7 days. He'd wasted away in front of Dean's eyes.

Dean pinched the bridge of his nose and willed his heart to slow down. The image of Castiel walking away was quickly replaced by Sam's withered body, his cracked and parched lips and his sunken face. Dean could feel his whole body tensing under the onslaught of emotion that enveloped his mind. “I can't lose you too, Sammy. I can't.”

Sam took a deep breath and let it out slowly. Dean's words had been barely above a whisper and it seemed to temper Sam's anger but the older man knew Sam wouldn't just roll over when his freedom was on the line. He heard Sam draw in a steadying breath before, “You won't, Dean. Just let me -”

“I said no.”

Dean's deep tone brooked no argument now, this time projecting so there would be no mistake. Sam squared his shoulders in defiance as he dumped what was left of his meal back into the pot. The brunette tried so hard to accommodate Dean's heavy moods but it was so aggravating never having his own opinions heard.

“Fine," he scowled, "I guess I'll just go read. Again.” Sam tossed his bowl and spoon into the wash bucket and stormed off to the small side-chamber they had built into a not-quite-library.

Dean sighed as he pressed his fingers in harder, short nails digging into the skin just beside his eyes. He remained there for a few minutes after Sam left before he realized he'd lost his appetite too and returned his breakfast to the pot. He put his dishes in the bucket as well before shuffling back into their shared bedroom to get dressed for the day. Sam didn't throw tantrums often, but that didn't suddenly mean they didn't need to eat so Dean had no choice but to put their worn-out argument on hold.

Trousers, boots, shirt, vest, gloves – done. Every item an off-shade of brown but it wasn't like he wasn't about to get sprayed by the sea anyway. Dean ran his hands through his short spiky hair a few times but as usual, his hair didn't want to play nice and remained partially mussed atop his head. Resigned to defeat, the blonde shouldered his work sack and headed toward the front door. Just as he was about to grab the handle Sam's voice carried out from the library.

“I worry about you too, you know.”

Dean's hand fell away from the portal and he took a few steps back to look into the other room. He didn't say anything in response, but he didn't have to. Sam knew he had Dean's attention.

The shaggy brunette continued to look at the book he was holding but his melancholy tone found Dean's ears just fine. “You're not the only one who lost Cas, Dean. Do you think I don't worry about you going out on those boats, too? I just want to be near you so I can know you're okay.” His eyes flicked up to catch his brother's, swirling pools of hazel that were marred by a sadness Dean tried so hard to ignore.

“Sammy, I-”

“I know. Just...” Sam took a deep breath, running his tongue along his lower lip absently. He looked back to his book, “Be careful.”

“Always, Sammy.”

A touch of a smile curled Sam's lips and he gave Dean a dismissive wave of his hand. “You're going to be late.”

Dean forced himself to smile back. He appreciated the out and took it with haste. He moved back to the front door and slipped through, breaking into a jog toward the shore the moment he felt the early morning sun on his face.


	2. Behold

Dean loved being out on the open ocean. There was something about the rolling waves beneath the hull and the endless horizon that made him feel at ease. Not to mention, not that he would admit it, this early in the day the sun dancing along the sea created such a marveling shade of blue that he could get lost in it for hours while the wind took them out to deeper waters. 

The trawler Dean crewed was one of 4 ships owned by a wealthy fish monger in Port Royal, Mick Davies. The ships worked in pairs, hauling great weighted nets between them to catch larger numbers of fish than their canoeing counterparts near the shore. It made for long days, but the payout grew to match as long as they made their quota. Today would be an easy day though – rather than netting their haul, Dean's ship, the Dusky Maiden, and their counterpart, the Song of the Sea, were coming out to collect the snapper pots they had put down the day before. The other two ships were further out, waiting for night to fall to start sweeping for herring.

The cries of “Hooked!” and “Pull!” rang across the deck as each pot was snared and reeled in. Dean was on the pull team so every time the command was shouted, all he had to do was grasp the thick rope in front on him and yank in time with the other hands to send the pots soaring into the air and over the deck where another team would quickly ease them down and unhook them to ready the line for the next pot. After just the first half-dozen pots, Dean was already starting to sweat through his shirt but that didn't slow him down. He knew what was at stake if he got kicked off the crew, not just for himself but for Sam.

It was just passing noon when the Dusky Maiden had finished clearing the pots and were getting ready to re-bait them and drop them back in the water. Dean pushed a pot overboard and waited to hear the satisfying splash but there was a distinct thunk before the sound of erupting water. He looked over the side, gripping the rail to keep from falling, and saw what looked like charred planks of wood drift by. At about the same time, another crew member called for the captain. Production stopped as the crew clamored for the port side to look into the water with Dean and the others. Sure enough, more smoking remains floated by, some still on fire where oil lamps had spilled. Then came the bodies.

Dean felt like the wind had been punched out of him as he stared at the figures bobbing in the water. He almost missed the call to return to their duties but the sharp crack of a whip broke him from his fixation. Somewhere between them and shore a battle had taken place and by the look of the tattered uniforms on some of the deceased, the brave men of Port Royal were not the victors. 

The captain called the full crew to the deck. There would be no sense putting down any more pots with the debris scaring off all the fish or the bodies being more enticing than their bait, but he wanted eyes out for survivors. They were going to follow the drift to see if they could be of any use getting anyone to shore, or, of course, finding any lost valuables.

What they found was the wreck of the HMS Ruby, smoldering and half sunk but no obvious signs of a battle. No canon holes or broken masts, just one gaping hole through the bow and smoke billowing from every porthole. One of the crew offered, “Looks like their canon powder stores caught. Bad luck, that.” Dean could only nod. He'd never been on a warship before so he had no idea. The trawlers never carried canons.

The captain ordered their two long boats lowered, two men in each, to ferry over to the HMS Ruby to look for survivors. Dean hopped in one with a scrawny fair-haired kid he'd gotten to know named Alfie. Alfie was just a little younger than Sam which is probably what caused Dean to take such a liking to him – that and his persistent smile and desire to help with whatever Dean was doing. Maybe, when they make it back to port, he should invite Alfie over for a change. Give Sam someone to talk to.

As Dean and Alfie made it closer to the wreckage, he could see movement on the deck and hear voices calling out to them. What he initially thought were calls for help, he quickly learned were cries for them to run, to save themselves. Confusion contorted Dean's features as he looked back at the Maiden, seeing if they were waving any flags, but the rest of the crew still stood at the rail looking at them with anticipation. A low whine from the HMS Ruby pulled his attention back just in time to see the wood splinter, to see bodies launched into the air, and to see the ship be seemingly sucked into the depths of the ocean amidst a cacophony of exploding timber and crunching bones.

Alfie screamed and scrabbled toward the back of the boat while Dean stared wide-eyed at the fountain of water that shot up where the warship used to be. Both men were coated in a fine mist from the spray but otherwise unharmed. After a moment all that remained were a few pieces of driftwood and gentle waves that rocked the longboat back toward the Maiden. It all had happened so fast. Dean couldn't tear his gaze away from the calming waters before him. There had been a ship there. There had been people on board telling them to run. Why run? What did they know? What happened? What the hell happened!?

After what seemed like an age, Dean was shaken from his reverie by the shouts of his crew behind him, some crying for them to return to the ship as fast as they could while others shouted at the captain to leave them. Dean looked at his hands wrapped around the oars, white knuckles straining against the wood as the voices returned to white noise and slowly began to row them back toward their ship. He never even noticed that their companion long boat was no where to be found.

Luckily, the ship waited and once they climbed back aboard the Maiden, two other crewmen wrapped Dean and Alfie in coarse blankets and ushered them below deck. Dean's nose scrunched up again in confusion. Why was he being taken below deck? It smells too much like fish down here. He hates it down here. But he also found himself not fighting back at all. It wasn't until he was seated on a bale of hay that he registered the sound of Alfie crying beside him. A moment later, a bottle of rum was being offered to him but when he reached to take it, his hands were shaking. Unable to pass off the bottle, the crewman set it at Dean's feet and went running back for the deck. More shouts to make ready and head for shore wafted below but Dean barely registered the sound. He stared at his shaking hands and slowly brought them to his face where he felt his own hot tears pouring down his cheeks. He was in shock.

“Son of a bitch.”

~*~

Dean can't remember how he got home. He woke up in his bed to light peeking through his window and the weight of Sam's arm across his chest. His first thought was that his little brother was an octopus, all clingy and sprawling limbs. His second thought was after he shifted and realized how ungodly sore his muscles were. He didn't think he had worked that hard the day before and started to go over the previous day in his head when it hit him. The ship, the screaming... He felt the tremors start again in his hands and pretty soon the rest of his body was trembling. Dean turned on his side to face away from his brother to try and hide the rising panic on his features. He wrapped his arms around himself and drew his knees upward to try to stem the shaking but nothing was helping.

After a moment, Sam's calm voice came from behind him as the hand now draped over Dean's arm began to gently stroke the dampening skin, “Tell me five things you can see.”

“Really, Sammy? Now?” Dean huffed a laugh but the quivering in his voice gave him away.

“Five things you can see, Dean.”

Dean took a deep breath to try and settle himself before looking around the room. “Door. Shoes... Dirt. A leaf. Pants.” He forced the rest of the breath out quickly and brought the heel of his hand up to rub his eyes.

“Good. Now four things you can feel.”

“Sammy...”

“Now.”

He drew in another breath, still trying to calm his shuddering body. “I can feel the sheets. I can feel my hair stuck to my face. I can feel my nails against my skin. I can feel your hand.”

“Good. You know the next one.”

Dean grit his teeth but tried to focus on Sam's hand still gently stroking his upper arm. Sam is there. Sam is ok. Focus on Sam. “I can hear you breathing. I can hear the breeze outside. I can hear me talking.”

“And then?”

“I can smell we both need a shower.”

Sam laughed, his exhalation tickling against the back of Dean's neck. “Yeah ok, but what else.”

Dean paused for a moment, drawing a long breath in through his nose. He tried to find another smell but as he screwed his eyes shut and brought both hands now back to his face, he realized there was only one scent clouding his senses. _I smell smoke._

The blonde could feel himself falling apart again. Where the shaking had almost disappeared, he felt it resurfacing with a vengeance. Sam seemed to feel this as well and his hand on Dean's arm tightened and pulled to roll him onto his back again. Dean uncurled as he was moved, straightening out his legs but keeping his hands covering his face. Can't let Sammy see him like this.

“Hey, well I know what you don't smell.” Sam waited for the noncommittal grunt from his brother before continuing. “Breakfast.”

Dean could hear the smile in Sam's voice and it pulled at the corners of his lips too. “As long as it's not breakfast stew..”

Sam let out another laugh as he pushed up from the bed. “Alright, alright. I'll whip us up something else.” He rolled over Dean and planted his feet on the floor. “And, uh, maybe you should take that shower before gracing the kitchen with your pungent presence.”

Dean reached out and slapped his brother on the back in retaliation and let his other hand fall from his face, rubbing it down over his mouth and chin, wiping away what he hoped was the only evidence of his tears. He found Sam staring at him, smiling but with a worried crease on his forehead. He forced a smile of his own, “I recall saying we both stunk to high Heaven so maybe you should go first.”

“What are you talking about? I smell fabulous.” To make his point, Sam raised his arms in the air so Dean could smell how truly odorous he was.

Dean groaned and brought his legs up to kick Sam off the bed, muttering curses and vague threats as a real smile crossed his face. Sam whooped and jumped out of the way, shielding his side and rear from the muscled limbs lashing out from beneath the covers.

“Ok, ok! Breakfast will be ready in ten, jerk.”

“Yeah whatever, bitch.”

The brothers exchanged smirks before Sam disappeared out the door, clicking the portal shut behind him.

Dean rubbed at his face again, still catching some residual wetness on his fingers, but he just sniffled and climbed out of bed. He wasn't sure how Sam always knew what he needed, but that kid had read so many books it was no real surprise he could go all brain doctor at the drop of a hat. The sensory grounding was something Sam introduced back when his nightmares about Cas had gotten really bad. It also always helped to have Sam right by his side. Perks to being poor and only having one bed, he guessed.

Once Dean heard sizzling coming from the main room, he stepped out the small side door into what passed as their wash room. There was a short wooden stool, a banded bucket, and a water pump with a cloth draped over the top. Royal trappings compared to some in the city so Dean didn't complain at the chill temperature that splashed at his feet as he pumped water into the bucket. Once the receptacle was full, Dean dunked the cloth in the clear water and sat down on the stool to begin wiping himself off. He took a whiff of his armpits and nearly choked. Maybe the smell hadn't been Sam after all. He made sure to scrub his underarms twice in apology.

When he was done, he leaned forward and dumped the remaining water over his head to rinse out the salt from his hair. He grabbed a dry cloth to start removing the residual moisture from his skin when Sam called that breakfast was ready. Dean yelled back that he'd be there in a minute and hastened to get dressed.

When he stepped into the main room there was the delightful smell of charred fish and scrambled eggs. The moan Dean let out as he approached the skillet nearly had Sam blushing, and the elder brother couldn't help smirking at his sheltered kin when he saw the red tint to his cheeks. Sam coughed quickly and pulled a filet and a portion of eggs off the fire and passed it to Dean.

“This is awesome, Sammy. Where'd we get money for eggs?”

Sam swallowed thickly as he pulled the rest of the food off onto his own plate, “Uh, the guys who dropped you off last night gave you a bonus, I guess.”

Dean quirked a brow as he shoveled the first bite into his mouth. He was going to ask more about whoever dropped him off but the flavor that hit his tongue had him making more obscene noises that caused Sam to flush.

Sam tried to laugh the awkwardness away, “Do you need a moment alone with that fish?”

“I might,” Dean fired back, barely able to hold back a chuckle himself. The food was damn good. “The hell did you put on this?”

“Nothing. This is just what happens when we actually get fresh food instead of day-old shit from the market.” Sam began eating his own piece and smiled.

Dean hummed appreciatively, “I should get attacked more often.”

That comment made Sam's face darken and his chewing slowed. Hearing about whatever happened the day before was not among the topics Sam seemed to be ready for. It then occurred to Dean that Sam might not know anything about what happened yesterday. For all he knew, his crewmen dropped him and a pouch of silver on their door step and left. Dean's mouth went dry at the thought of having to tell Sam about what happened and he struggled to swallow the bite of egg. As usual, Sam wasn't one to disappoint.

“Dean... what happened yesterday? The guys mentioned something about a monster but that couldn't be right. Right?” Sam questioned, popping another bite of the filet in his mouth as his brows drew together in concern. 

Dean shrugged, trying to play it off. “Who knows. We were all probably suffering from sun stroke or something. It was probably just the Spanish being dicks again.” He pushed the food around his plate with his fork, suppressing a shiver that wanted to run down his spine. Yeah, the Spaniards... that's all it was. No guttural cries from the depths or whole warships being sucked into the dark abyss. Just a normal, human enemy and fatigue playing tricks on his mind.

Dean managed to fork one more bite into his mouth before setting his plate down. “Welp, I should get going or I'll miss the boat.”

Sam seemed to panic, nearly dropping his plate as he abruptly stood. “What? You're going to work?” His eyes widened as he looked at his brother, disbelief evident.

“Well, yeah. It's not like we're going to get money for free,” Dean scoffed at the notion. “It's nice that they gave us some compensation for the bullshit yesterday but it's not like they're going to keep hand-feeding us.”

Sam tried to make an argument, citing the nightmares and his near panic attack this morning but Dean waved him off. “Sam, enough. I'm good. Are you good?” He fixed his brother with a knowing look, eyes squinted just slightly with one brow raised. He hadn't forgotten their conversation from yesterday about how Sam worries about him too. Sam held Dean's gaze as he chewed lightly on his bottom lip. There was fear in those big brown eyes, but Dean couldn't just abandon the only job he's managed to keep down. Finally, Sam gave a small jerk of his head in affirmation before casting his eyes to the ground.

“Good,” Dean followed up, stepping forward and clapping his brother on the shoulder. “We only got to set half the pots yesterday so I should be home early. Don't wander too far and be safe.”

Sam's head perked up, “Don't... I can go out?”

Dean didn't miss the hope in those words. “Yeah, sure. I mean, if you're going to be worrying about me, I might as well be worrying about your tall ass getting run over by a cart or something too.”

The brunette grinned, feeling a bit better about the unfolding events but the mirth didn't quite break the mask over his eyes. Dean would just have to take what he could get.

~*~

When Dean reached the docks, he looked for his crew but found a completely foreign group getting the Dusky Maiden ready to sail. He stood at the end of the dock, trying to puzzle out what the hell was going on when he heard a surprised voice rise behind him, “Oh! Mr. Winchester!”

Coming down the shore was a man Dean had only met a handful of times. He was short with close-cropped dark hair and a charming British accent. He waved cautiously as he approached as if he was unsure how to interact with one of his employees.

“Mr. Davies.”

“Oh please, call me Mick. You know that.” The shorter man made to punch Dean amicably in the arm but aborted the gesture mid-swing, turning his hands toward his fine-pressed suit jacket. “So, uh, you came back to work?”

Dean thought it sounded like his boss was trying to make a statement but it came out questioning. “Uh, yeah. Is that so odd? I mean, our contract says -”

“I know what the contract says.” Mick pursed his lips as he ran his tongue over his teeth. He continued to fiddle with the buttons on his jacket, a nervous gesture Dean had seen him partake in when they'd had a meeting regarding increased pirate activity in the bay.

Dean huffed a laugh, “Sir, I can assure you I am fit to crew. The incident yesterday was -”

“You're dismissed.”

“What?” Dean's steely gaze met Mick's and the business man seemed to shrivel under his stare.

“I, uh, you can't work any of my ships anymore. I can't have you scaring off the new crew. The rest of your men already resigned so I figured you would too.”

Dean stood in silence. Dismissed? Because he might scare the crew? He narrowed his eyes and grit his teeth. If he was going to fight for his job he couldn't lose his temper. “Sir, if -”

“Good day, Mr. Winchester.”

Mick abruptly turned and scurried back down the shore as the new crew of the Dusky Maiden called out their final preparations and pushed away from the docks. Dean could only stand there and stare at the sand drifting over the wooden planks where Mick had just been. Yesterday he had nearly died and today he swallowed his fear only to get dismissed. What was he supposed to tell Sam?

Dean walked back to their shack in a daze. He'd only been gone about a half-hour but Sam was already nowhere to be seen. Poor kid is cooped up whenever Dean isn't with him so of course he would have taken off the moment he was allowed to. The blonde slowly unbound his laces and toed off his boots before wandering into the bedroom and collapsing face-first onto the bed. He'd done no actual work today but he was exhausted, as if the weight of the morning's events were physical burdens on each of his limbs. He couldn't even muster the strength to shift the pillow beneath his head or rearrange himself in some semblance of comfort. Maybe he'd just suffocate lying face down in the sheets. Maybe...

_Sammy..._

“Fuck...” Dean mumbled into the cloth before pushing himself over onto his back so his legs bent to the floor. He felt sick. What was he going to do? He'd already been kicked out of most of the establishments in town due to either drinking, fighting, or wenching and now the ships were off-limits thanks to Mick. Mick didn't own all the boats, of course, but whatever rumor that was flying around about whatever they might have saw surrounding the HMS Ruby would have him and the rest of the old crew blacklisted for years. He could always go back to the docks in a different capacity. It wasn't like he hadn't done it before when they fell on hard times.

Dean's spiraling thoughts were broken by the sound of the front door slamming open and then being roughly closed. He hadn't thought he'd been laying there long, but cracking open his eyes he could see twilight through the window. Sam crashed through the kitchen area and braced himself on the door frame, breathing heavily and staring at the prone figure on the bed.

“Really Dean!? A kraken!?”

Dean propped himself up on his elbows, face creasing in worry. A kraken? What?

“The hell are you talking about?”

“Yesterday,” Sam fell the rest of the way into the room and knelt beside the bed, one arm supporting himself on Dean's knee. He had to pause to catch his breath. “Yesterday, on the Dusky Maiden, you saw a kraken.”

Dean flopped back onto the bed, keeping his eyes fixed on the patchwork ceiling. “I didn't see shit, Sammy.”

“Yes, you did.” Sam hauled himself up and crawled next to his brother, hovering over him with a hand on his chest. “I stopped by the tavern on my way home and it was all anyone was talking about. There was some poor kid in the corner so deep in his cups I don't think he even knew his own name. He just kept blubbering about the kraken.” He let out a short laugh. “I thought he was crazy at first, just another sailor who saw a giant squid, but Dean, it was your whole crew. One of the guys finally gave me the story about how your ship came face to face with a monster and that YOU,” he slapped his hand against Dean's chest, “were in a freaking row boat! What the hell, Dean!?”

“Sammy, it wasn't that bad. There was no monster.” Dean had to work to keep his breaths even. He could feel his hands start to tremble where they laid at his sides.

“Two of your crew DIED.”

“They must have fallen overboard looking for loot from the Ruby. There was nothing, Sam.”

Sam slid his hand from Dean's chest and grabbed his wrist instead, holding it up between them. “If there was nothing, what are you so afraid of?”

Dean's eyes flicked down to his raised hand where Sam's stable grip made the shivers of his own muscles more prominent. He jerked his hand back and rolled away from his little brother. “It's just mind games. There's no such thing as a kraken. I'll be fine.”

He heard Sam sigh behind him as he sat fully on the bed. “I also heard the whole crew was replaced.”

Dean squeezed his eyes shut. He knew how screwed they were but he had hoped to spare Sam the worry until he had a plan.

“You're out of work. The money they left wasn't a bonus, it was severance.”

Hearing it said aloud knocked the wind right out of him and for a moment he felt like he was drowning.

“But it's ok.” Sam took a deep breath which made Dean instinctively draw in air again as well, “because I actually kind of have a job.”

Dean bolted upright and turned to Sam. He had a job? Since when? Dean thought he was fixing his brother with a trademark glare but Sam just laughed.

“I can't tell if you're relieved or if you want to punch me,” Sam smirked but seemed to catch the underlying question. “I've been working for the Magistrate for a while. They know my situation so a scribe would bring me case documents and books to go over once you left and then retrieve them when they saw your ship coming to port. The Magistrate actually visited me once to congratulate me on my work in the Savoy Twins Murder and said that if I kept this up and was ever well enough to leave the house, I could be sworn in by the British Court and they'd actually start paying me.”

Dean clenched his jaw as he received the new information. His little brother was going to be a lawyer? He wasn't sure if he should be pissed or proud. He didn't realize how long he'd just been staring until Same piped up again.

“Say something. Anything.”

Dean coughed to clear his throat and finally turned away. “Uh, good work, Sammy.”

Relief flooded Sam's face. “I still won't leave the house without you, of course.”

Dean just waved his hand. “It's whatever. You're probably right. You're fine. Plus, if you don't show up in person they won't pay you, right?”

The older Winchester could hear the grin splitting his brother's face. “I won't let you down, Dean.”

Dean huffed, “Yeah yeah, enough of this touchy feely crap. Go make dinner.”

“Don't you think you should make dinner? Since I am the one bringing home the bacon now?”

“I don't know. Do you want food poisoning?”

Silence hung for a moment while Sam seemed to ponder his brother's counteroffer before clicking his tongue, “Good point,” and left the room.

Dean gave a short laugh as he laid back on the threadbare sheets. His dorky kid brother, a freakin' lawyer. He felt like he should be angry or hurt that his brother was keeping such a secret from him, but he couldn't help just being proud. Worried, but still proud. His thoughts were starting to drift back to the catastrophe that was the day before when Sam's voice called from the other room that food was ready. He'd have to leave his self-pity party for another time.


	3. Penance

The next morning felt like Hell. 

Dean stood near the fading fire in an undershirt and pants while he watched his baby brother walk out the door to begin his job in earnest. He tried to smile and be supportive, to let the pride he felt show through, but no amount of faking made the image of Sam's withering body disappear from behind his eyes. What if the strain brought on an episode again? What if staying indoors and calm really were the only reasons he hadn't had an episode in so long? All of the 'what if's in the world didn't matter when the front door snicked shut.

Dean rubbed his hands down his face and turned to get ready for the day. Sure, Sam had a job and all but it didn't mean Dean could be a lay about. After dinner last night, Sam had tried to convince him to stay in and rest, that he needed to recuperate after the trauma he experienced but of course Dean had scoffed at the idea. If he was traumatized, which he wasn't, he needed to get back in the proverbial saddle and get over it. He wasn't some dame who needed a good cry in bed.

Pulling on his tri-point hat, Dean headed toward the center of town.

Port Royal was a bustle of activity mid-morning as Dean weaved his way through the crowds. His aim was Bela's Tavern, owned by one bougie Bela Talbot. He'd worked for her as a barkeep several years ago and hoped that perhaps she'd let bygones by bygones and give him another chance. And if she didn't? Well, he would be within spitting distance of a stiff drink.

Dean had to stoop a little walking through the open entrance way of the tavern and looked around as he straightened. A petite woman with auburn ringlets draped over her shoulders was idly drying a tin mug behind the bar. When he stepped in, her eyes immediately fixed on the blonde and she set the mug down to brace her hands on the counter top. The dulcet tones of her posh accent rang over the general din, "Well, fuck me. Dean Winchester."

The blonde laughed at the woman's choice of words. "Now Bela, we both know what happened when I tried that."

Bela pressed her plum painted lips together to hide her grin as Dean walked over, "Yes, and I do believe I said never to set foot in here again. Did I not?"

Dean rapped his knuckles on the wooden counter, "No, no, you're right, but I was hoping we could put that little, uh, misunderstanding behind us if you were looking for some extra hands around the bar." He attempted to turn on the charm with one of his deadly smiles but Bela was having none of it.

"Dean, love, as much as I'd like to, my girls would be far too distracted to get their own work done," Bela pursed her lips as she glanced over Dean's shoulder at one of the servers, a young black haired woman in a corseted dress who was making doe eyes at Dean and very nearly clipped a patron in the head with her tray. Dean glanced behind him at the woman and gently took his lower lip between his teeth before giving her a wink. 

Just as Dean was getting to appreciate the flush that crept up the woman's neck, a loud bang on the counter pulled his attention back forward. A tall mug of ale sat sloshing onto the bar top and Bela was giving him a mischievous smirk. "See what I mean? As an apology, have a drink on me. When you're done, get the fuck out of my bar." 

Dean chuckled and sipped his drink as Bela walked back to the other end of the counter to resume drying dishes. He figured the answer was going to be no, but there was no harm in trying. And definitely no harm in the view. Dean held his pint as he turned to brace his back against the bar so he could see the lone waitress flitting about the few brunching customers. She was certainly pleasing to look at but...

When the girl had finished putting the last of the meals on the tables, she almost tip-toed up to the blonde man before placing a hand gingerly on his chest, "Could I interest you in one of our specials?" She batted her long lashes over her deep teal eyes.

Dean set his near-empty cup down beside him and wrapped one arm around her slender waist as he brought his now free hand up to her chin, tipping her head back so he could gaze down into her eyes. He leaned in as if to kiss her tenderly but as the woman's eyes closed, he veered to the side so his lips came to rest beside her ear.

"They're the wrong blue."

The woman's breath hitched as Dean pulled away. He caressed her cheek with his thumb as he disentangled himself and stepped away from the bar. As he made for the exit, he raised a hand to bid the establishment farewell, "Thanks for the drink, Bela."

~*~

Throughout the day, Dean tried a few of his other old haunts to ask about work. The blacksmith turned him down. So did the carpenter. Even the baker threw him out. He contemplated the office of the East India Trading Company. If Sam was going to be working for the British government, why couldn't he swallow his pride and become a trader? He kept it in the back of his head, but would see what tomorrow held first. For now, he needed a stronger drink than the swill Bela had given him that morning and a solid distraction from his failures as a big brother.

Shortly after nightfall, the ex-fisherman found himself in a seaside tavern boasting a sign that read 'Sailor's Hide-Away". He had downed three shots of rot-gut in quick succession before a large hand fell on his shoulder. Dean jumped and spun around, reaching for his knife when the offending figure came into view.

"Woah there, brother, easy now."

Dean huffed, tucking his short knife back into the small sheath concealed just inside his waistband as he sat back down, "Fucking hell, Benny."

The burly Cajun laughed and clapped Dean on the shoulder again, "Didn't mean to spook ya, Dean. Just came to see what this heavy drinkin' was about. Haven't seen ya down rum like that in a dog's age."

Dean groaned as he spun back to the bar and lifted his empty glass toward the bartender. He didn't need a lecture. Benny took the stool beside him and leaned his elbows on the counter, "I heard about the boat."

"Not you too." 

Benny raised his hands in defense, keeping his gaze on the opposite wall rather than his friend, "Ya don't have to explain anything to me, brother. Jus' worried about ya."

Dean swiped his hand down his face and sat up straighter when the barman came over to refill his glass. He downed that one quickly too and Benny let out a sigh. 

"Have you even eaten anything?" Benny asked.

"Nope. I've got no job. I've got no money. So I eat no food," Dean replied as he gestured to the bartender again.

Benny's jaw clenched at that and Dean knew he caught on to his plan. Dean had known the bear of a man for a few years before he signed onto Mick's crew, and it was actually because of Benny that he even got the job. Benny was one of the crewmen on The Song of the Sea and when he heard their partner ship had an opening, he threw Dean's name in for consideration. Over the years together, Benny had learned many of Dean's habits, especially his self-destructive ones. Like the plot for tonight. Run up a tab, don't pay it, and get the daylights beaten out of him. Dean knew this plan rather well and as a result, so did Benny.

"I love ya, brother, but you need to figure out a better way to cope." Benny stood from his seat and laid a heavy hand on Dean's neck, massaging the muscle underneath before letting his arm fall away. It was obvious Benny wasn't looking to be dragged into a fight and with the brawl likely imminent, he paid up his own bill and made a hasty exit.

~*~

Dean awoke to gentle hands rolling him over but he didn't immediately open his eyes as he took stock of the situation. He was still drunk. His face was crusted with sand, his clothes wet and clinging to his skin. His hat was gone. His jaw was sore but so were his hands. His -

"I know you're awake."

A familiar voice reached his ears as a strong finger flicked his nose.

"Ow, dammit Sammy." Dean's hand flew up to cover his face, spraying sand through the air.

The younger Winchester chuckled as he began lifting Dean, one arm under his shoulders and the other behind his knees.

"Aw, Sammy, I didn't know you cared." Dean joked as he tried to wipe the grime from his eyes, thankful for his brother's help to get home. However, rather than heading up the beach he heard the waves getting louder and before he could make the connection he was dropped and enveloped by water.

The night time sea was frigid and a shock to the blonde's system. Dean came up a second later, sputtering and staggering toward dry land. Sam was right there, knee deep in the water with him and quickly put steadying hands on his arms. Dean coughed and swiped his hair from his face, "Dammit, Sam."

Sam snorted, "It's what you get for losing me my first day's pay. Let's get you home."

Dean winced when his brother wrapped an arm around his torso to help support him on their trek home. Nothing broken, but it felt like he was being stabbed by a thousand knives where Sam's fingers curled against his ribs. With the initial shock subsiding, Dean subtly leaned into the ache. His brother thought he was just a bit off-balance and held tighter and Dean relished the painful sensation. _I deserve this,_ he thought.

When they entered the shack and Sam deposited his brother on the bed, it was the first time that night Dean really got a look at Sam. There were bags under his eyes and his whole body was tense. His hair was partially falling from the tie and sticking to his sweat slick skin. 

Dean sat on the edge of the bed as he took off his shoes, "So how was work?" 

"Work... work was great, but then I came home to an empty house and I couldn't find you anywhere." Sam braced himself in the doorway, wearing an expression Dean lovingly nicknamed his 'bitch-face.' 

"But you found me," Dean grinned lopsidedly at his brother as he started to peel off his sea-soaked clothing. 

"Yeah, by paying off your debt so they'd tell me what they did with you. They threw you off the docks, by the way. I was convinced you'd drowned." 

_Ah..._ Dean stopped undressing once he was down to his pants. So that's why Sam looked like death warmed over. He felt the guilt take hold in his chest as he turned away. "Sorry, Sam." 

Sam huffed, "As if." The taller man stepped forward and started grabbing his pillow and blanket from the bed. 

Dean threw down his collected clothes in the corner and rounded on Sam, "Oh come on. We're not an old married couple. Put your stuff back." 

"No, Dean," Sam straightened and glared at his older brother, "You are a kind, caring, wonderful person and I can't stand to see you do this to yourself. To me. Cuz you want to know something? Work sucked and I needed to talk to you about it because, hey! I've never had a job before, but you weren't here. How about you stop being a martyr and just be my brother?" 

The exasperation in his voice broke Dean's heart as he watched Sam head toward the study but he had nothing to say. Sam was right. He messed up. Again. He pinched the bridge of his nose as he felt the impending hangover coming on and turned from the door way to crawl in bed. No matter how tight he wrapped the covers around himself, the empty space beside him left him feeling cold. But he deserved this too. He deserved all of it. 

**Notes for the Chapter:**

> There will be pirates. I promise. Just gotta get the brotherly angst out of the way and then we're off to hunt a Kraken.


	4. The Mission

The next morning brought one hell of a hangover.

Dean groaned as he pulled the sheet over his face to try and block out the late morning sun. The muted cacophony from outside told him it was way past when he should have woken up. Sam was probably already gone. Of course he didn't even say goodbye.

Slowly, he pulled the covers down and rolled onto his back. A glance to the side showed a cup of water in the middle of the floor, where Dean wouldn't step on it, and a small slip of parchment. Dean grimaced as he rolled off the bed and crawled to the offering. He downed the water gratefully and then picked up the note.

_Dean,  
I will be back just before sun down. Please be home and just take it easy today. I left you a bland breakfast but eat slow. If you throw up on my side of the bed I will kill you._

_Sam_

Dean smirked as he crumpled up the paper and threw it off to the side before pulling his feet under him. Breakfast sounded like the worst thing in the world right now but he knew getting something in his stomach would benefit him in the long run. Still clutching the cup, he made his way out into the kitchen where he found a clear basin of water to procure a refill and a plate of bread and some depressing looking fruit. Just as he was ripping a chunk of bread to choke down, a loud banging came from the front door.

"Dean! Hey it's me, open up!"

Dean's brow quirked in surprise, "Benny?"

The blonde shuffled to the door and opened it wide, squinting at the light pouring through. Benny stood leaning heavily on the wall beside the door trying to catch his breath. He pulled his cap off and wiped the sweat from his eyes. "You're gonna wanna see this. Go get some trousers on."

Dean quickly looked down at his state of undress as a faint blush crept across his cheeks, "Uh, yeah. Right. I'll be right out." He slammed the door shut, wincing as the sound echoed in his aching head while he staggered back into his room to get ready. When he reemerged a minute later, both men were better composed and Benny led the way down to the docks.

~*~

Dean saw the smoke long before they reached the shore but what greeted him, drifting just beyond the pier, still made his chest tighten. What was left of The Dusky Maiden had been towed into port. The busty figurehead remained but it looked like the rest of the ship had been riddled with canon fire. It was a wonder the craft was still afloat. They watched as the tow lines were dropped from The Song of the Sea but no one was making to board the wreckage.

Dean swallowed thickly, "Any survivors?"

Benny shoved his hands deep in his pocket, the silence that stretched between them just as telling as what finally came from his lips, "Not a single body was even found."

The blonde concentrated on controlling his breathing and schooled his expression. That was almost him on that boat. Maybe he should thank Mick for firing him after all. Despite his own disbelief in his last experience at sea, he felt the tremors start before asking hopefully, "Pirates?"

Benny grit his teeth,"Dean, you know -"

"Fuck, Benny," Dean threw his hands up and turned from the sight, fingers gripping his hair too tightly as he started a brisk pace back into town, eyes on the dirt path.

He heard his friend turn and start to come after him but they both stalled when a confident, no-nonsense voice boomed from the white doors to their right, "Mr. Winchester! Step into my office."

Dean glanced up to the smartly dressed man standing in the doorway to the East India Trading Company's headquarters. His perfectly combed dark hair was complimented by a blindingly white smile that, though charismatic, made it clear his statement was not a request. Dean spared a glance at Benny. The burly sailor shrugged and gave a nod toward the building, just as confused as Dean so the blonde clenched his jaw and made for the pristine building. Any dealings with the East India Trading Company were bound to be unfortunate.

Once inside, Dean followed the man to a plush office. There was a map table spread out in the center of the room and at the far end a desk, littered with parchment and all manner of writing utensils. It wasn't Dean's first time in this particular office but the owner of the room had been absent for a low-level meeting with simple fishermen. When the man sat down at the desk, Dean gulped in realization. "Y... you're Richard Roman?" He was rendered speechless. The man that sat before him held every life in Port Royal in the palm of his hand.

The man smiled again and steepled his fingers over the desk, "Please, call me Dick."

Dean managed to not snicker but only because of the weight of what was happening. His growing headache and the scene of The Dusky Maiden now coupled with a meeting with the head of the East India Trading Company didn't leave a lot of room for mirth. Dean shuffled uneasily as he covered his mouth and coughed gently to clear his throat, "Ok, uh... Dick... What can I do for you?"

"I'm glad you asked, Mr. Winchester," Dick flattened his hands atop the loose documents. "I have a problem, and I want you to fix it."

"O-Of course. What's the problem?" _Please don't hurt Sammy._

The sneer that contorted Richard's lips made Dean's stomach drop, "One word, Mr. Winchester. Kraken."

Dean's blood ran cold as his airways constricted. He took an involuntary step back. _No... nononononono-_

"It was brought to my attention that you are the only person to have seen the kraken and both lived and not totally, pardon my phrasing, lost his shit. I believe this makes you the best suited to undertake this task. You are a man of the sea, after all. Are you up for it, Mr. Winchester?"

Dean wanted to knock the pearly teeth from the man's perfect smile but needed to not pass out first. The kraken wasn't real. He didn't see anything. How could he hunt something that didn't exist? He must have been silent too long as Dick repeated his name and Dean sucked in a deep breath, refocusing his gaze on the regal figure. "Huh? Uh, o-of course, Mr. R- Dick." _Nonononononononono..._ "But how am I even supposed to find it? Who would even give me a ship?" There's no way this 'mission' was even doable.

If anything, Dick's smile widened, "Great questions. I knew you were a smart man." Dean's lips twitched at one corner in acknowledgment of the compliment but it did nothing to assuage his fears. "The Song of the Sea will take you to Tortuga where they will give you funds, provided by me, to hire a ship and crew. You have leave to chose the best men and vessel at your discretion. I will also provide you with an assistant to make sure the plan proceeds. Mr. Ketch?"

From the open doorway a sturdy man with similarly perfect dark hair, wearing a long black coat entered. He fiddled with a small knife, cleaning what Dean hoped was dirt from beneath his fingernails.

"Mr. Winchester, this is Arthur Ketch. He will support your efforts to remove our little problem and act as my liaison where financing is concerned. Is this agreeable to you?"

Dean looked from Ketch back to his new employer but found his vocal cords were no longer cooperating. They were really going to send him out to sea to hunt a beast that pulls whole frigates into the depths.

"You look alarmed, Mr. Winchester. Are we going to have a problem ourselves? Perhaps I could send a message up to the Magistrate to draw up a proper contract so we're clear?"

Dean didn't miss the threat that seeped into Dick's smile or the light chuckle from his new partner. Dean coughed again, "No, sir. No problem." _Don't you fucking touch Sammy._

"Fantastic. Wonderful. Your next step after acquiring a crew and vessel will be to find a certain pirate by the name of Gabriel. He calls himself "The Trickster' but he has a very powerful tool in his possession that allows him to maintain that moniker. A compass."

Dean managed a short laugh, "A compass? Really? I mean, I have a compass. No need to go chasing after some lame ass pirate."

Dick's hands tensed over the desk, "This compass is special. It points to whatever the holder wants most."

The blonde ran a hand through his hair, scratching at the back of his head, "Well, that won't do me much good. What I want most is dead." _There has to be a way out of this..._

Dick's smile disappeared, "Mr. Winchester, it is in your best interest to want to kill the kraken most."

Dean's mouth ran dry, "Y-yes. Of course." He let his hand drop back to his side as the other man's radiant smile returned.

"Great. Super. Your ship leaves in fifteen minutes."

Dean's eyes grew wide, "Oh, uh, if I could just pack some-"

"Not necessary, Mr. Winchester. We took the liberty of packing for you and loaded everything onto the ship."

"But S-"

"Mr. Ketch, please escort our fine young representative to his ship. Good luck, Mr. Winchester."

~*~

The sun had barely passed it's zenith when Dean found himself staring out at nothing but open ocean, Port Royal beyond the horizon behind him. Despite his years sailing, his stomach churned and he found himself losing any sustenance he managed to force down. Sam was going to come home that night to a ransacked home and no sign of Dean. He'll have no clue what happened and probably think he'd been kidnapped, murdered, or pressed into slavery. Dean covered his face with his hands as he leaned on the railing. At least he hadn't seen Ketch since boarding. The guy gave him the creeps.

Benny, on the other hand, had checked in on Dean whenever he could; bringing him small bits to eat or just distracting him from the shit show his life had suddenly become. The one thing they didn't talk about was the actual mission at hand. Dean wouldn't be able to take it if they did. 

As the sun was setting Dean remained top side. There'd be no way he could sleep. Not without Sam and certainly not with..... _it_ lurking in the depths. He tried to think of what advice Sam would give. The kid was so freakin' smart he'd certainly have the answer to their predicament. He was so much like their dad.

Dean didn't think of his parents very often, John and Mary Winchester. Long ago he'd lost the point of remembering. It only hurt and Sam barely remembered them so why bring them up? Their mom had died when Sam was only 5. It had been a stormy night and Sam wouldn't stop crying so their dad had gone to fetch a doctor. When he returned, their house was ablaze, struck by lighting, and Dean sat huddled under the eaves of another building with Sam cradled to his chest. Their mom didn't make it. After that, their dad crawled into a bottle and never came out. Dean has done what he had to do to protect Sam ever since. 

Before the catastrophe, though, John had been a hunter on both land and sea. A fearsome force to be reckoned with. Whether it was a deer, a fish, or a pirate John knew how to kill it and could. Dean had a healthy respect for his father before the drinking started and learned a lot. It's what allowed the boys to survive on their own for so long. But this? Hunting a mythical beast? He wasn't sure it was even something the mighty John Winchester could take on.

With the cool night air in his lungs, Dean focused himself and thought back to his years with his father. He luckily only vomited once more, but by morning's light he knew he had two options.

Continue on this suicide quest to kill the kraken or -

Kill Arthur Ketch.


	5. Murder

Dean knew he couldn't wait until they made port to take action. They'd sailed through the night which gave him a little over a day to exact his plan before they reached Tortuga and he was going to need help. As the morning's duties were underway, Dean sought out Benny.

The Cajun bear was laying pitch along one of the outer rails when Dean found him. The blonde leaned gently on a dry section of wood, acting as relaxed as possible before, "I'm going to kill Ketch," slipped casually from his tongue.

Benny continued painting on the dark, thick sealant without even a hitch to his stroke, "I know. 'Bout time."

Dean pursed his lips to hide his smile. He should have known Benny knew what was going through his head already.

"So what's the plan?"

Dean looked down to his boots, running his tongue along one of his pointed canines, "Tonight. Quick and dirty."

"Mmhm, and?"

Dean let out a quick breath in exasperation, "What do you mean 'and'? And then we tell the captain to turn this boat around and we go back to Port Royal."

"Mmhm."

"What, Benny? Spit it out." Dean's jaw tensed as he turned to his friend. He was keeping his voice low to not draw attention to them but Benny was being frustrating to a point where he was finding it hard to handle.

Benny drew in a deep breath but otherwise continued his duties as normal, "You know Ketch sleeps in the captain's quarters, right?"

"Yeah."

"With the Captain."

"So what?"

"Who is paid by Mick Davies."

"Benny..."

"Who is on the East India Trading Company's take."

"What the fuck, Benny?" Dean's waning composure broke and he ran a hand down his face, stopping while his palm covered his mouth. He stared across the deck and out into the open waters. 

"Look, I knew you wouldn't have taken the fishin' job if you'd known and you needed the money." Benny dropped his brush into the dark bucket and braced his hands below the rail, tipping his head down to look at the creaking deck beneath his feet. "I didn't do it maliciously. You of all people should know that."

For several seconds only the sounds of the waves breaking against the hull passed between them. Dean thumbed his nose and sniffed, coughing gently as he looked over Benny's head to the helm of the ship and the captain beside the wheel, "Just... just distract the captain tonight and I'll handle the rest. I'll deal with whatever comes after."

Dean walked off before Benny could agree with or reject his plan. He would have to trust that his friend would come through. But... how could he have tricked him into the employ of the Trading Company? Well, not tricked. He'd just left out that little detail. Dean wandered below deck and back to his bunk to continue brooding with a degree of privacy. 

On one hand, Benny was right. He and Sammy were on hard times back then, not that Sammy had been totally aware. Dean always had a perfectly logical explanation as to why he suddenly had money or extra food even if he didn't have a proper job. He'd seen it in Sam's eyes, now and then, that he was suspicious but he never pressed the issue. In the end, he trusted Dean to not do anything stupid enough to get arrested. When Benny had mentioned the job on the Dutch-built trawler he'd jumped on it with no question. Maybe a few questions would have been pertinent... Dean sighed and rubbed at his face again. _Too late for those questions now, idiot. Maybe next time you'll ask if your employer spirited away your dad before you accept._

Dean was thirteen when men in blue coats and yellow vests swooped into their home in the middle of the night and dragged a drunken John Winchester into a barred carriage and sped off into the darkness. Throughout it all, Dean could only gently cover Sam's mouth and hold him tighter as his brother woke to the sounds of struggle. Dean just mouthed over and over, 'Just look at me, Sammy. Just look at me,' until the men had gone. He'd been terrified but not stupid. There was nothing he could have done to stop his dad from being taken. Then, the following day, it was as if no one had ever even heard of John Winchester. He never told Sam what had happened either, just that he must of had a nightmare and their dad was out looking for his next drink. Over the years, whenever John had come up, Dean just brushed it off and said the man must be dead by now. For all he knew, he was.

~*~

Night fell once again over The Song of the Sea and Dean was strolling along the main deck, his hands clasped loosely behind him to keep from fidgeting while he waited for Benny. Hours passed, and just as Dean was passing the door to the cabin for the umpteenth time, Benny came running up from below deck, holding his cap to his head as he rushed to wake the captain. Benny pulled up short and knocked as gently as he could and still rouse the man in charge. After all, he did have a guest that likely wouldn't take to be woken up. Not to mention a sleeping Ketch would be easier to kill than a woke Ketch.

Dean ducked into the shadows as the door swung open. It was dark inside meaning the occupants had been slumbering but the captain was still fully dressed. Though looking a bit disheveled, the captain was composed when addressing his crewman, "What is it, Master Lafitte?"

"Beggin' yer pardon, captain, but yer gonna wanna see this." While Benny attempted to match the captain's civility, there was a degree of panic in his voice and wide eyes as he turned and made back for the lower decks without waiting for an answer or a chance for the captain to waylay him with further questions.

Benny didn't spare a glance for Dean as he ran by, the captain quickly following, and disappeared down the steps. Dean took that as his chance to slip through the still open door and close it quickly behind him. With the portal shut, the room was plunged back into near blackness save for the glossy illumination of the moon through the side windows. He pressed his back to the wood and waited for his eyes to adjust, scanning rapidly for any sign of movement that could mean Ketch was onto him. Once he could view the room in detail, he pushed off the wall and slipped his knife from his belt.

On the far side of the room rested a simple bed and a covered lump within. Dean moved forward slowly, placing each foot deliberately as he approached the bed with his knife at the ready. As he stepped up to the cot and pulled his arm back to strike, he realized just in time that the mass in the bed was not human and there was a rustle of cloth just to his right. Jumping back, he narrowly avoided a dagger to his neck as Ketch's arm shot out of the darkness.

Dean immediately rushed back in, moving to grab the extended arm and thrusting his own blade toward Ketch's abdomen. Ketch's arm was seized but he dodged the strike, bringing his free arm down to trap Dean's arm between his bicep and side. A quick shift had Ketch holding the arm just above the elbow and a abrupt upward motion dislocated Dean's shoulder and forced his knife to clatter to the floor. Dean gasped in pain and released Ketch's other arm, stumbling backward into a small side table and knocking the unlit candles to the floor as he unexpectedly found himself sitting down. Ketch sheathed his dagger fluidly as he surged forward. Dean brought his hand up to try and deflect him but he was batted away easily before Ketch's strong hand was gripping against his bruised ribs.

Dean cried out but was swiftly silenced by a hand over his mouth, "Now now, Mr. Winchester, to what do I owe the assassination?" Ketch's thick British accent slid down the blonde's face.

Dean tried to wrestle free but Ketch's hand just tightened, bringing tears to Dean's eyes, "What, you didn't think I knew about your little tussle at the bar?" Ketch chuckled when Dean grimaced. Of course someone like Ketch knew he was injured.

"But let me guess. You are unhappy with our arrangement and want to return to Port Royal and your precious brother and thought the easiest way to do that was by removing your watchdog. Am I close?" Ketch's sneer had the blonde closing his eyes. He'd failed and now Sam was at risk. To Dean's surprise, Ketch released him and straightened, pulling his own clothes back into a semblance of order. "Mr. Winchester, I'm going to let you in on a little secret. I don't like this deal any more than you do and could I not be here, I would." He leaned back in, placing one hand on Dean's shoulder and the other on his upper arm. "Do try to be quiet." He jerked his hands in opposite directions and a soft pop accompanied Dean's wearied groan.

Dean opened his eyes but couldn't bring his gaze to meet his adversaries, "What do you mean you don't like it? Then just leave."

"Hm, maybe you're not as bright as Dick thought."

The blonde smirked. No, no he wasn't.

"Well, that's not my problem for now, so do be on your way so I can get some sleep. And know that if Dick doesn't receive a letter with my mark on it every two weeks he will kill your precious Sam. Now, good night, Mr. Winchester." 

Ketch motioned for the door and Dean stood, a bit wobbly, and clutched his shoulder. He had nothing more to say to the Company Slave, at least nothing nice, so he wearily exited the room. When the door closed again behind him, the weight of his failure settled in. The open ocean air had no hope of turning back into the over-bearing fish smell of the docks at Port Royal, or the subtle flowery scent of Bela's Tavern. Just as Dean was starting toward the lower deck, the captain came up the steps mumbling to himself and soon disappeared into his quarters. At the bottom of the steps stood Benny. Their eyes met briefly before Benny turned away. Sadness and disappointment awashed the sailor's features as he slipped back into the shadows below desk. He knew. Dean chewed on his lower lip and cast his gaze to his boots as he moved back to his bunk to wallow in his shame of defeat.


	6. Tortuga

Dean barely slept a wink after his disastrous attempt to free himself from this mission. He couldn't get what Ketch had said out of his head, that he didn't want to be here anymore than Dean did. But he was an agent of The East India Trading Company. He was obviously paid very well to do whatever it was he usually did. Following some guy around playing at sea monsters must be a piece of cake. Then again, Dean's only dealings with Ketch so far had been when he received his contract and then trying to kill him. They were both stuck in this together, maybe he should give him the benefit of the doubt after all.

Mid-morning found the Song of the Sea pulling into port at the lawless city of Tortuga.

By daylight, the trading town looked almost respectable. Merchants hawked their wares in the streets and sailors from all walks of life ambled the broken cobblestones. The smell was the first clue for Dean that this was not somewhere he wanted to stay long. Day trips on the Dusky Maiden made for some ripe-smelling crewmen but it was nothing compared to scent of stale sewage wafting down the docks.

Benny met Dean one last time at the gangway and grasped his hand in parting. 

"I'll look out for Sam. Don't you worry none. Just focus on gettin' back home."

"I know you will, Benny. Thanks."

It did little to ease the churning in Dean's stomach, but it was all the reassurance he was going to get that Sam would stay safe in the clutches of the East India Trading Company. After his little chat with Ketch the night before, he was terrified now if anything happened to Ketch's letters. It'd mean death for his baby brother. He hoped, if worse came to worst, Benny would be able to sneak Sam out of Port Royal and keep him hidden. Having been a smuggler before meeting his wife in the British colony, if anyone could hide Sam, it was Benny.

Arthur Ketch brushed passed the pair, "Let's do keep the bro moments to a minimum. I don't want to stay in this den of degenerates any longer than I have to."

Dean and Benny chuckled, hand's still twined, unwilling to let the finality of the salutation set in.

"It's alright, brother. We'll all get through this and some day look back on this whole adventure as a fond memory."

"Benny..."

"C'mere," Benny tugged on Dean's hand and pulled him into a tight bear hug. Dean resisted at first, arms awkwardly splayed to the sides but this was possibly the last friendly interaction he'd ever have. The blonde screwed his eyes shut as he returned the gesture fiercely. When he pulled away, he saw moisture brimming in his friend's eyes and the man fought back a sniffle.

"Oh c'mon now, Benny," Dean tried to joke but the words were catching in his throat.

"Tch, look in a mirror before you go gettin' on my case," Benny laughed and clapped him on the shoulder. "You best be gettin' on now. Mr. Ketch looks none too pleased."

Dean glanced back over his shoulder at the dour man waiting for him on the dock who, for once, was wearing plain clothes. Whatever had Ketch embroiled in this mission had him eager to get it over with.

Dean stooped to pick up his satchel and swing it over his shoulder, sparing one last look at Benny, "I'll see you on the other side."

Benny nodded sharply, pursing his lips to hold back everything else he wanted to say as Dean turned and disembarked. 

~*~

Though Ketch usually looked the part of a noble, he seemed to know his way around the town surprisingly well. When Dean asked, he claimed it was because he had consulted a map and actually prepared for their task on the journey over instead of "mucking about with the riff-raff." Dean didn't totally believe it. With the town in this state of decay, there was no way a map would remain accurate for more than a couple months. Another chapter in the enigma that was Ketch, Dean supposed.

A brisk walk brought the pair to a three-story tavern. The first floor was riddled with tables and patrons in varying states of consciousness. The second floor was visible as a balcony to one side and stairs disappeared up a hallway from there leading to the third floor. The air smelled a mix of vomit and citrus that nearly brought tears to Dean's eyes but he noticed his partner had no issue with the cloying scent. Ketch led them over to the bar, passed a small table with two older men sitting behind it sharing a subdued conversation. As Ketch began gently interrogating the barkeep, one of the elder men laughed. Dean spun in place, looking back at the older pair before striding closer. His approach caught the men's attention and they both looked up at him when he came to a stop.

"Bobby?"

The man on the left was a shorter fellow with his brown hair slicked back and turning grey over his temples. He'd grown himself a bit of a gut since Dean last saw him, but there was no mistaking his father's old hunting partner. The man to the right was a taller man with dark brown skin and pierced ears, his hair shaved down but he sported an impressive mustache and goatee. Both looked in need of a good wash and were giving Dean the stink-eye.

Bobby leaned back in his chair, "What the hell are you doing here, boy?"

The man beside him edged forward, "You know this kid?"

Bobby grumbled under his breath and gestured vaguely at Dean and then to the other man, "Rufus, this is Dean. Dean, Rufus."

Dean reached out his hand, "It's a pleasure to meet you, sir."

Rufus took his hand with a grin, "No it's not, kid. And don't call me 'sir'."

Bobby's shoulders shook with silent laughter as Dean drew back his hand but when he looked back at the old hunter, Dean saw a look of worry.

"But really, what are you doing here? Where's Sam?"

Dean scratched the back of his head, rubbing his hand down to let it rest on the back of his neck, "It's a bit of a story."

Rufus kicked his feet up on the table and folded his hands behind his head, chair teetering on two legs, "Well good. We don't leave 'til nightfall so regale us."

Dean spared a look over at Ketch who was keeping one eye on him while he continued questioning the barkeep but didn't seem too concerned with where their topic of conversation was going. Mostly sure it wouldn't get him in trouble, Dean told the older men about the HMS Ruby, proud of himself for mostly maintaining his composure, about the Dusky Maiden, and finally about his quest to kill the kraken. He left out his attempt to kill Ketch, of course.

"Well you're in luck, kid," Rufus smirked.

"Don't, Rufus," Bobby scowled at his friend.

"Don't what?"

"Well, you need a crew and a boat to find The Trickster. We are part of a crew with a boat and a lead on The Trickster. You'll just have to come with us on one little pit-stop."

"What? Really? That's great!" Dean returned Rufus' grin, finally feeling some hope for this doomed journey.

"Dean..." Bobby rubbed a hand down his face, scratching at the stubble on his chin, "You do know where you are, right?" Dean nodded. "And you get who- what- we are?"

Dean hadn't wanted to think about it, but if they were slumming it in Tortuga...

"You're pirates," Dean finished. "But so what?"

"If you sail with us, that makes you a pirate too, kid," Rufus slipped his feet back to the floor and rocked forward, "A wanted man."

Ketch chose that moment to turn up behind Dean and placed a hand on his shoulder, "I can assure you that won't be a problem. Who is your captain and where can I find him?"

Bobby and Rufus both laughed at that, much to Ketch's chagrin. Rufus wiped a tear from his eye, "Well, right now we don't have a captain. We crew the big girl ourselves until we can pick up the captain from his, ah, vacation."

Bobby snorted and took a swig from a flask he produced from his vest pocket.

Ketch grit his teeth and Dean could tell it took a lot of effort not to roll his eyes, "Very well, what is your vessel and when do we leave?"

Bobby pushed his seat back and stood, stowing the flask away for later, "She's a gutted merchant ship. We leave at dusk."

Rufus similarly stood and made to tip his hat before realizing he wasn't wearing one. He smirked at the mistake and sauntered out of the tavern. Bobby gave them a small wave before also exiting. 

Dean turned and brought his hand up, thumping Ketch on the chest, "Now look'it that. Not doin' so bad, am I? Already got us a crew and a ship to go after Gabriel."

Ketch looked down to his crinkled shirt and flicked away the invisible flecks of dirt Dean's hand might have left, "Yes, quite."

The blonde beamed with his success and turned to find some fresher air. Though he was growing used to the putrid stench of the tavern, his lungs longed for the crisp salty air of the shore.

While the docks didn't provide much relief, he did manage to snag some decent dried meat and bread on his way down and the strong breeze allowed him to eat without gagging. Ketch simply followed, taking up residence on a barrel next to Dean and pulling his own snack from his satchel. Dean leaned back against the rotting building, chewing slowly as he considered what now lay before them.

Pirates. Of course they were going to crew with pirates. No one else would be foolish enough to go looking for The Trickster let alone take on a kraken. The blonde sighed. His father would tie him to a post and whip him for this. He hunted pirates. He hated pirates. How dare his son become one?

_But I am **not** a pirate. Just because I sail with them doesn't make me one. Right? I haven't committed any crimes... And Ketch said it doesn't matter anyway. I'm sure I'll be pardoned if I succeed. Ugh... 'if'...._

"Mr. Winchester, if you think any louder you're likely to alert the Spanish Navy."

Dean barked out a laugh, "Sorry, man. Kind of hard not to have a lot on my mind right now."

"Quite. But there's nothing to be done about it now so you might as well enjoy the last moments of peace we're going to see for some time."

Dean blew out a long breath of air. Ketch was right. The moment they boarded the ship with Bobby it was going to be chaos. He was placing all his trust in the grizzled old hunter, both that he was telling the truth about Gabriel and that the boat he was getting on wasn't crewed by men who were going to slice his throat the moment he fell asleep. Maybe the crew was the least of his problems. What if he got scurvy and died anyway? What if they hit a reef and all died? Then Ketch's letters would stop. What if-

"Mr. Winchester."

Dean deflated further against the sodden wood, "I know, I know." He rubbed his now empty hands over his eyes and smoothed back his hair.

The two men sat there until night began to fall. As torches and lamps were lit, Bobby and Rufus came to find them and lead them to the small row boat that would take them out to deeper waters where their ship anchored. A few other men joined them in the dingy before they pushed off. In the fading light, Dean didn't see the dark ship pull around the cove. It wasn't until they were just about upon the ship that he heard a loud fluttering as black sails unfurled and he turned to behold The Black Pearl.


End file.
